Saudade, roughly translated as longing or nostalgia for the past, is at the heart of Portugal’s famed Fado music. As two or three guitar players gently pluck the strings, a fadista (female fado singer), purrs and wails, giving complex and heartfelt expression to songs of bittersweet remembrance, of love lost, of death. Watching such a performance is a sublime experience and offers a window into the very soul of Lisbon, which also seems to cast its eyes backwards more than forwards.

Europe’s smallest capital was, after all, the seat of power for one of the three most powerful seafaring nations on earth in the 15th and 16th centuries. Much of what visitors prize today was created during that period and just afterwards. And it often seems as if Lisbon missed much of the 20th century, as well; held in the grip of a dictatorship during World War II and for years afterwards, it sidestepped many of the modernizing trends that swept Germany, France, Italy, Great Britain and other European nations. It’s catching up now, with an economy that’s going great guns. But what the visitor will find gripping—and can experience in 24 hours—is the sense of living history here, of a city that’s still enmeshed in centuries long gone.

8 a.m. - 9 a.m.: Who knew breakfast could be such a grand event? You'll feel like a modern-day Marie Antoinette as you're sipping your Licungo (a specialty of the house, a black tea from Mozambique) and nibbling on pastries at the Pastelaria Sala de Cha Versailles. A Lisbon institution since it opened in 1932, its original décor of stained glass windows, marble floors and weighty chandeliers has faded a tad, but remains eye candy of the first order.

9:30 a.m. - 12:30 p.m.: Monks, sailors and a view are the goals of your morning amble around the Praça do Império. Order doesn’t matter but be sure to give yourself enough time to explore the Mosteiro do Jeronimós(the final resting place of Vasco de Gama and an important example of “Manueline” architecture, which combined elements of both the Gothic and the Moorish and added lots of frills and curlicues); the Museu do Marinha, which is set in a wing of the monastery and is devoted to Portugal’s storied seafaring past; and the 16th century Torre de Belem, one of Portugal’s most potent symbols. The tower itself is wedding cake-ornamental, and nearly as pretty as the panorama of the harbor and city you’ll see from up top. If you rush (or skip one of the attractions above), you may have time also to work in a visit to the nearby Museu Nacional des Coches, Lisbon’s most popular attraction. More interesting than it sounds, it houses a number of ornate horse carriages, most from the 17th through the 19th century.

Morning Alternative
Get art-smart at the Museu da Fundação Calouste Gulbenkian, a former private collection of extraordinary richness. Among the many treasures here (some actually purchased from Russia’s Hermitage Museum!) are two Rembrandts, a notable Rubens, illustrated medieval manuscripts, antiquities from across the Mediterranean, and priceless Chinese vases.

12:30 p.m. - 2 p.m.: Where else but the “Fish Dock” or Doca Peixe, as the restaurant is named as well as located, would you head for the freshest of sea food? Codfish is the specialty both here and throughout Portugal, and comes with a chorus line of clams and a draping of fresh coriander. Or you can choose your own fresh catch from the tanks with live critters at the front, and they’ll throw your pick on a charcoal grill or bake it in salt, in a jiffy.

2 p.m. - 6 p.m.: Get lost in the Alfama district. A warren of slender cobblestone streets, weather-beaten taverns, baroque churches and bustling street markets, it’s a time machine for sailing back several centuries, a deeply picturesque and fascinating area to wander. Make time, in particular, for a stop at the Castelo de Sao George, a moated castle where peacocks roam and swans glide, its an oasis of serenity in this bustling neighborhood (the views from here are first rate, too).

Afternoon Alternative
If you’re a fan of the so-called Flemish Primitives, head to the Museu Nacional de Arte Antiga. Yes, you heard that right: Portugal’s most important museum houses some of the most famous paintings of Bosch and Memling, along with masterworks by Zurbarán, Velazquez and Dürer.

6 p.m. - 8 p.m.: Discover the pleasures of port. The Solar do Vinho do Porto, the Port Wine Institute has been holding daily tastings in an 18th century palace since just after World War II, and with 300 varieties on tap, you’re sure to find one that pleases your palate.

8 p.m. - 11 p.m.: Foodies know to go to Nariz do Vinho Tinto and you should follow their example. After all, it’s run by one of the most powerful gourmands in the country, Matos Cristovão, editor of the Portuguese version of the Spanish food-bible Epicur. Whether you go with the house-cured ham, a crackling venison sausage or the cod with sautéed onions which has been roasted in ham fat until it simply explodes on the tongue, you’re sure to leave with a renewed respect—if not awe—for Portuguese fare.

11 p.m. - on … Diva Maria da Fe runs one of the most respected fado clubs in Lisbon and it is here where you should head to cap of the evening (and perhaps greet the dawn, as some Fado sessions go on all night). Called Senhor Vinho, it’s become “The Apollo” of Fado, a place where not only top names like Ms. Da Fe perform, but up and coming talent are discovered.

With teams using more than 100 unique apparatuses to launch globular projectiles a half-mile or more, the 27th annual World Championship Punkin Chunkin event is our pick as November’s Weird Festival of the Month.

Pauline Frommer is the creator of the new Pauline Frommerguides in bookstores now. Her book, Pauline Frommer's New York, was named Best Guidebook of the Year by the North American Travel Journalists Association.

Mosteiro do Jeronimós is located at Praça do Império, phone 21/362-00-34; www.mosteirojeronimos.pt. Open from 10 a.m. - 6 p.m. from May to September, only until 5 p.m. the rest of the year. Admission to the church is free, but the cloisters are 4.50€ ($5.60) adults 26 and older, 2.50€ ($3.15) adults and children 15-25, free for seniors 65 and over and children under 14.

Museu do Marinha, phone 21/362-00-19,is located within the Mosteiro de Jeronimos (see above) and shares the same hours. Admission is 3€ ($3.75) adults, 1.50€ ($1.90) students and children ages 6-17, free for seniors (65 and over) and children under 5.

Torre de Belemis also at the Praça do Império, phone 21/362-00-34; www.mosteirojeronimos.pt. Tues-Sun 10 a.m. - 6 p.m. between May and September, until 5 p.m. the rest of the year. Admission is 3€ ($3.75) adults, 1.50€ ($1.90) for adults 15-25 years, free for children under 14 and for seniors (65 and over). On Sundays admission is free until 2 p.m.

Castelo de Sao George, Rua da Costa do Castelo, phone 21/887-72-44; www.egeac.pt. Open daily 9 a.m. - 9 p.m. from April through September, until 6 p.m. the rest of the year. Admission 3€ ($3.75) adults, free for children under 10

Pauline Frommer is the creator of the new Pauline Frommerguides in bookstores now. Her book, Pauline Frommer's New York, was named Best Guidebook of the Year by the North American Travel Journalists Association.

The grand tradition of the gap year: that glorious time between school and work when young people take an extended break to see the world, explore their options and, perhaps, get a better sense of how they want to live the rest of their lives. These days, more people facing middle age are wondering why young people should have all the fun.